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$215+ Cheap flights from Midland (MAF) to Caribbean

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/13. Fares are subject to change and may not be available on all flights or dates of travel.
MAF — SJU
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
1 adult, Economy
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Cheap flight deals from Midland to Caribbean

Cheapest flights from Midland to Caribbean
Explore the most affordable flight options available from Midland to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 27, 2026.

This United Airlines deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/412:02 pm
MAF
-
SJU
1 stop7h 36m
United Airlines
Fri 5/87:20 am
SJU
-
MAF
2 stops16h 35m
United Airlines
Deal found 1/27$260
This United Airlines deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/212:07 pm
MAF
-
SJU
1 stop7h 19m
United Airlines
Wed 3/48:30 am
SJU
-
MAF
2 stops15h 33m
United Airlines
Deal found 1/27$280
This Southwest deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/22:55 pm
MAF
-
SJU
2 stops7h 45m
Southwest
Wed 3/45:40 am
SJU
-
MAF
2 stops12h 35m
Southwest
Deal found 1/27$352
This United Airlines deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/2912:05 pm
MAF
-
SJU
1 stop7h 33m
United Airlines
Thu 4/21:40 pm
SJU
-
MAF
1 stop9h 35m
United Airlines
Deal found 1/26$369
This Southwest deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/41:00 pm
MAF
-
SJU
2 stops9h 25m
Southwest
Fri 5/86:50 am
SJU
-
MAF
2 stops15h 55m
Southwest
Deal found 1/27$373
This American Airlines deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/296:07 pm
MAF
-
SJU
2 stops13h 53m
American Airlines
Wed 4/11:30 am
SJU
-
MAF
1 stop9h 12m
American Airlines
Deal found 1/26$382
This Southwest deal was found by Cheapflights users on 1/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/92:55 pm
MAF
-
SJU
2 stops7h 45m
Southwest
Fri 2/133:15 pm
SJU
-
MAF
2 stops10h 35m
Southwest
Deal found 1/25$506
This Southwest deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/295:30 am
MAF
-
SJU
2 stops9h 45m
Southwest
Thu 4/210:05 am
SJU
-
MAF
2 stops9h 55m
Southwest
Deal found 1/26$526
This American Airlines deal was found by Cheapflights users on 1/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:48 pm
MAF
-
MBJ
2 stops18h 53m
American Airlines
Thu 6/45:17 pm
MBJ
-
MAF
2 stops17h 51m
American Airlines
Deal found 1/25$550
This American Airlines deal was found by Cheapflights users on 1/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/298:27 pm
MAF
-
MBJ
1 stop19h 46m
American Airlines
Wed 6/312:47 pm
MBJ
-
MAF
1 stop11h 25m
American Airlines
Deal found 1/25$593
This American Airlines deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/278:29 pm
MAF
-
SJU
1 stop16h 44m
American Airlines
Mon 3/27:01 pm
SJU
-
MAF
2 stops15h 47m
American Airlines
Deal found 1/27$596
This American Airlines deal was found by Cheapflights users on 1/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/146:20 pm
MAF
-
MBJ
2 stops18h 07m
American Airlines
Mon 3/303:04 pm
MBJ
-
MAF
1 stop27h 07m
American Airlines
Deal found 1/25$683

Find flight deals from Midland to Caribbean

Keep the following information in mind while searching for Midland to Caribbean flight deals. Data was last updated January 27, 2026.

Round-trip from

$260
(United Airlines)

One-way from

$215
(United Airlines)

Popular in

July

Cheapest in

April

Average price

$480
From Midland Intl to Caribbean
Search Deals
One-way flight from Midland Intl to Caribbean
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($38 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midland to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 27, 2026.
Use the filters below to find and compare flights from Midland to Caribbean that are best for you.

Fly from

Midland

Fly to

Caribbean

Route

Depart

Return

Price

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Mon 5/4

7:00 am-3:42 pm

1 stop7h 42m

San Juan Luis Munoz Marin Intl

Fri 5/8

2:55 pm-11:15 pm

1 stop9h 20m

$260

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Mon 5/4

8:24 pm-4:32 am

1 stop7h 08m

San Juan Luis Munoz Marin Intl

Fri 5/8

11:59 pm-9:42 am

1 stop10h 43m

$260

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Mon 3/2

7:40 am-6:25 pm

1 stop8h 45m

San Juan Luis Munoz Marin Intl

Wed 3/4

3:46 pm-9:44 pm

1 stop7h 58m

$260

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Mon 5/4

1:00 pm-11:25 pm

2 stops9h 25m

San Juan Luis Munoz Marin Intl

Fri 5/8

2:00 pm-11:10 pm

2 stops10h 10m

$352

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Mon 3/2

2:55 pm-12:40 am

2 stops7h 45m

San Juan Luis Munoz Marin Intl

Wed 3/4

5:40 am-4:15 pm

2 stops12h 35m

$352

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Sun 3/29

12:05 pm-8:38 pm

1 stop7h 33m

San Juan Luis Munoz Marin Intl

Thu 4/2

1:40 pm-10:15 pm

1 stop9h 35m

$369

MidlandMontego Bay

MAF - MBJ

MAFMBJ

Midland Intl

Fri 5/29

6:48 pm-1:41 pm

2 stops18h 53m

Montego Bay Sangster Intl

Thu 6/4

5:17 pm-11:08 am

2 stops17h 51m

$550

MidlandMontego Bay

MAF - MBJ

MAFMBJ

Midland Intl

Fri 5/29

6:48 pm-1:41 pm

2 stops18h 53m

Montego Bay Sangster Intl

Wed 6/3

12:47 pm-12:12 am

1 stop11h 25m

$550

MidlandMontego Bay

MAF - MBJ

MAFMBJ

Midland Intl

Sat 3/14

6:20 pm-12:27 pm

2 stops18h 07m

Montego Bay Sangster Intl

Mon 3/30

3:04 pm-6:11 pm

1 stop27h 07m

$683

MidlandMontego Bay

MAF - MBJ

MAFMBJ

Midland Intl

Sat 3/14

5:25 pm-1:05 pm

1 stop19h 40m

Montego Bay Sangster Intl

Mon 3/30

4:12 pm-11:15 pm

2 stops31h 03m

$709

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/25

Showing 1-10 of 14 results
1
2

Best time to book a flight from Midland to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Midland with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Midland to Caribbean

What is the cheapest month to book a flight from Midland to Caribbean?

Currently, April is the cheapest month in which you can book a flight from Midland to Caribbean (average of $247). Flying from Midland to Caribbean in July is currently the most expensive (average of $668). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated January 27, 2026.
Read through reviews of airlines operating flights from Midland to Caribbean, such as Southwest, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,268 reviews

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,268 reviews
Southwest
8.0
Very good
4,268 reviews

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,205 reviews
Southwest
8.0
Very good
4,268 reviews

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,197 reviews
Southwest
8.0
Very good
4,268 reviews

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Midland to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Midland to Caribbean?

    Most people fly from Midland Intl (MAF) if they book a flight from Midland to Caribbean. Midland Intl is conveniently located just 8.2 mi from Midland’s city center.

  • How long is the flight from Midland to Caribbean?

    Airlines like United Airlines and American Airlines fly from Midland to Caribbean in about 7h 08m. The time it takes to get you to your destination can typically vary by up to 34m. The distance from Midland to Caribbean is about 2432 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the most popular routes from Midland to Caribbean?

    The most popular flight routes from Midland to Caribbean are Midland Intl - San Juan Luis Munoz Marin Intl, Midland Intl - Montego Bay Sangster Intl and Midland Intl - Oranjestad Reina Beatrix.

  • Can I find deals for flights from Midland to Caribbean that include hotel bookings?

    Yes. In addition to deals on Midland to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midland to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midland to Caribbean.

  • Can I find deals for business class flights from Midland to Caribbean?

    Yes. Cheapflights offers flight deals from Midland to Caribbean by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Midland to Caribbean?

    Currently, April is the cheapest month in which you can book a flight from Midland to Caribbean (average of $247). Flying from Midland to Caribbean in July is currently the most expensive (average of $668). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Midland to Caribbean

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Top 3 airlines flying from Midland to Caribbean

Discover the top 3 airlines that operate flights from Midland to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$307Average$657FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$353Average$532FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$520Average$590FlexibilityNo cancel feeOn-time63%

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